Emails Stuck in Outbox

Issue/Question

My Outlook is not working properly

Messages in my outbox are not being delivered

Sent emails are remaining in the Outbox instead of sending

My emails are stuck in the outbox and won't send

I cannot send or receive messages, there is just a red 'X'

My Outlook keeps showing items I send as stuck in my Outbox.  However people respond to the email, so I know that the majority of them are sending.  

Error: Outlook has detected an issue with an add-on and has disabled it

Error: Not Responding

Environment

• Microsoft Outlook
• Outlook 365
• Exchange Online
• Microsoft Windows

Cause

Multiple Causes

Resolution

1. Restart Outlook
2. Restart Computer
3. Log into Outlook Web Access (OWA)
4. Open Sent folder
5. Compare Outlook Outbox and OWA Sent folder
6. If emails were sent, delete emails in Outbox
7. Repair Microsoft Office
8. Recreate Outlook Profile